MiMeDB: Showing metabocard for Methionine sulfoxide (MMDBc0000401)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:56 UTC

Update Date

2022-08-31 06:06:49 UTC

Metabolite ID

MMDBc0000401

Metabolite Identification

Common Name

Methionine sulfoxide

Description

Methionine sulfoxide (MetO) or L-Methionine sulfoxide belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Methionine sulfoxide arises through the oxidation of methionine residues in proteins by reactive oxygen species (ROS). Oxidation of methionine results in a mixture of the two diastereomers methionine-S-sulfoxide and methionine-R-sulfoxide. Methionine oxidation is considered an important post-translational event in protein synthesis and can affect the function and activity of many proteins. The oxidation of methionine plays an important role in vivo, during biological conditions of oxidative stress, as well as for protein stability in vitro. For instance, the oxidation of methionine residues in tissue proteins can cause them to misfold or otherwise render them dysfunctional. Most organisms have developed systems to restore these oxidized methionine residues back to methionine (i.e., converting MetO to Met). This reduction is done by the methionine sulfoxide reductase (MSR) system, with the MSRs type A (MSRA) and type B (MSRB) being specific for the S and R forms of MetO, respectively (PMID: 28917052 ). In mammals, the selenoprotein MSRB1 plays an important MetO repair function, and its expression is tightly regulated by dietary selenium (PMID: 28917052 ). The eventual proteolyis of any unfolded or misfolded MetO modified proteins leads to the production of free methionine sulfoxide that can be detected in blood or urine. MetO is not a proteogenic amino acid and cannot be incorporated into proteins during ribosomal mediated translation. Levels of free MetO are closely correlated with levels of oxidative stress. Methionine sulfoxide (MetO), increases with age in body tissues, and its presence is believed by some to contribute to biological aging. Levels of MetO are also increased in individuals suffering from chronic bacterial infections (tuberculosis) or other conditions causing inflammation (PMID: 32123207 ). Similarly, MetO is increased in the serum/plasma of patients diagnosed with sepsis (PMID: 27501420 ). This likely reflects the high production of ROS species arising from the overactive (but underperforming) immune response.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
L-Methionine sulfoxide	ChEBI
Methionine S-oxide	ChEBI
L-Methionine sulphoxide	Generator
Methionine sulphoxide	Generator
Methionine sulfoxide, (R-(r,s))-isomer	HMDB
Methionine sulfoxide, 35S-labeled, (+-)-isomer	HMDB
Methionine sulfoxide, (S-(r,s))-isomer	HMDB
Methionine sulfoxide, (2S)-isomer	HMDB
Methionine sulfoxide, (2R)-isomer	HMDB
Methionine sulfoxide, (+-)-isomer	HMDB
DL-Methionine sulfoxide	HMDB
L-Methionine S-oxide	HMDB
Methionine sulfoxide	HMDB

Molecular Formula

C₅H₁₁NO₃S

Average Mass

165.21

Monoisotopic Mass

165.045964392

IUPAC Name

(2S)-2-amino-4-methanesulfinylbutanoic acid

Traditional Name

L-methionine sulfoxide

CAS Registry Number

Not Available

SMILES

CS(=O)CC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10?/m0/s1

InChI Key

QEFRNWWLZKMPFJ-YGVKFDHGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Sulfoxide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfinyl compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methionine S-oxide (CHEBI:17016 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	54 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.6	ChemAxon
logS	-0.49	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.34 m³·mol⁻¹	ChemAxon
Polarizability	15.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-6639ef576db5a01f8ee5	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0910000000-4231d540eda02eebe871	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-f0849e8acf9a3e1e2763	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-004i-1910000000-b7a64800b9e577e219d4	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1910000000-b7a64800b9e577e219d4	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-a5138c4f03667c81645c	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-b8f17a35f754f6a2adff	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-40d23196cb4ee1cad23f	2019-05-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9400000000-cac8577601b69f1b723a	2019-05-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-43361da834d0b07907fd	2019-05-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-6090b56aa5a22d72fb4f	2019-05-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03kc-9400000000-f71dc9c687b7114eed8b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-9100000000-b03227c3dde8ee858ffb	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9500000000-a4583e8c3a4365d330e2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ff3de228e84a6b4470bc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9400000000-7375ade3d9a2e79890d4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-4fa3654466563449190c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-375f7404d6c31bdf96b3	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2019-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2019-05-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2019-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2019-05-22	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Epidermis
Feces
Placenta
Saliva
Urine

Tissue Locations

Epidermis
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192170	Mitochondrial peptide methionine sulfoxide reductase	Enzyme	Q9UJ68	Homo sapiens
MMDBp0195893	Methionine-R-sulfoxide reductase B2, mitochondrial	Enzyme	Q9Y3D2	Homo sapiens
MMDBp0195894	Methionine-R-sulfoxide reductase B3	Enzyme	Q8IXL7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0024768	Water	L-Cysteine	Peptide methionine sulfoxide reductase MsrB	Reduction	RHEA	34755880
MMDBr0024769	L-Cysteine	Water	Peptide methionine sulfoxide reductase 2	Reduction	RHEA	34755880
MMDBr0025389	Water	Methionine sulfoxide	Protein-methionine-sulfoxide reductase catalytic subunit MsrP	Reduction	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Sepsis		Association	Human Blood	HMDB	26847922
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	2	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	2		1.4	18	uM	Adult (>18 years old)	Both	Sepsis	HMDB	26847922
Human Urine	Detected and Quantified	0.31		0.14	0.66	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			0.6	3.59	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	1.48	0.80			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	1.67	0.69			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Feces	Detected and Quantified	110	80			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	20	10			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	4.0		3.0	5.0	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	12576054
Human Urine	Detected and Quantified	0.5038	0.5427			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.6418	0.4235			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			0.00	7.88	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Saliva	Detected and Quantified	0.0444	0.0842			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.110	0.126			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	3.28	1.20			uM	Adult (>18 years old)	Both	Normal	HMDB	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.30	1.40	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002005

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022789

KNApSAcK ID

Not Available

Chemspider ID

139840

KEGG Compound ID

C02989

BioCyc ID

CPD0-1959

BiGG ID

Not Available

Wikipedia Link

Methionine sulfoxide

METLIN ID

6428

PubChem Compound

158980

PDB ID

Not Available

ChEBI ID

17016

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

O'Donohue TL, Charlton CG, Thoa NB, Helke CJ, Moody TW, Pert A, Williams A, Miller RL, Jacobowitz DM: Release of alpha-melanocyte stimulating hormone into rat and human cerebrospinal fluid in vivo and from rat hypothalamus slices in vitro. Peptides. 1981 Spring;2(1):93-100. doi: 10.1016/s0196-9781(81)80017-4. [PubMed:7243627 ]
Boudier C, Cadene M, Bieth JG: Inhibition of neutrophil cathepsin G by oxidized mucus proteinase inhibitor. Effect of heparin. Biochemistry. 1999 Jun 29;38(26):8451-7. doi: 10.1021/bi9828526. [PubMed:10387091 ]
Mashima R, Nakanishi-Ueda T, Yamamoto Y: Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Anal Biochem. 2003 Feb 1;313(1):28-33. doi: 10.1016/s0003-2697(02)00537-7. [PubMed:12576054 ]
Schallreuter KU: Functioning methionine-S-sulfoxide reductases A and B are present in human skin. J Invest Dermatol. 2006 May;126(5):947-9. doi: 10.1038/sj.jid.5700086. [PubMed:16619011 ]
Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
Tarrago L, Oheix E, Peterfi Z, Gladyshev VN: Monitoring of Methionine Sulfoxide Content and Methionine Sulfoxide Reductase Activity. Methods Mol Biol. 2018;1661:285-299. doi: 10.1007/978-1-4939-7258-6_20. [PubMed:28917052 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Cho Y, Park Y, Sim B, Kim J, Lee H, Cho SN, Kang YA, Lee SG: Identification of serum biomarkers for active pulmonary tuberculosis using a targeted metabolomics approach. Sci Rep. 2020 Mar 2;10(1):3825. doi: 10.1038/s41598-020-60669-0. [PubMed:32123207 ]
Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]

Showing metabocard for Methionine sulfoxide (MMDBc0000401)

MOL for #<Metabolite:0x000055d24b1e23a0>

3D MOL for #<Metabolite:0x000055d24b1e23a0>

3D SDF for #<Metabolite:0x000055d24b1e23a0>

3D-SDF for #<Metabolite:0x000055d24b1e23a0>

PDB for #<Metabolite:0x000055d24b1e23a0>

3D PDB for #<Metabolite:0x000055d24b1e23a0>

SMILES for #<Metabolite:0x000055d24b1e23a0>

INCHI for #<Metabolite:0x000055d24b1e23a0>

Structure for #<Metabolite:0x000055d24b1e23a0>

3D Structure for #<Metabolite:0x000055d24b1e23a0>